3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

Base Information

Chemical Name:3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine
CAS No.:664966-33-0
Molecular Formula:C₄₃H₄₈N₂O₁₂S
Molecular Weight:816.926
Hs Code.:

Synonyms:3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

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Chemical Property of 3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

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Technology Process of 3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

There total 9 articles about 3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

: 664966-32-9
3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3',5',6'-tri-O-benzyl-3'-C-vinyl-β-D-allofuranosyl)thymine

: 3-N-benzyloxymethyl-5,6-dihydroxy-5-methyl-1-(2'-O-methylsulfonyl-3',5',6'-tri-O-benzyl-3'-C-vinyl-β-D-allofuranosyl)pyrimidine-2,4-dione

: 664966-33-0
3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

: 3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(S),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

: 3-N-benzyloxymethyl-5,6-dihydroxy-5-methyl-1-(2'-O-methylsulfonyl-3-C-(1,2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)pyrimidine-2,4-dione

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tert-butyl alcohol; at 50 ℃; for 19h;
DOI:10.1039/b307667a

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 664966-33-0
3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

Guidance literature:: Multi-step reaction with 4 steps

1: DBU / acetonitrile / 18 h / 20 °C

2: 6.32 g / NaOMe / methanol / 16 h / 20 °C

3: 91 percent / pyridine / 1.25 h / 20 °C

4: 31 percent / aq. OsO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol / 19 h / 50 °C

With pyridine; osmium(VIII) oxide; sodium methylate; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b307667a

Reference yield:

: 100-39-0
benzyl bromide

: 664966-33-0
3-N-benzyloxymethyl-1-(2'-O-methylsulfonyl-3-C-(1(R),2-dihydroxyethyl)-3',5',6'-tri-O-benzyl-β-D-allofuranosyl)thymine

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide / 1 h / 50 °C

1.2: 99 percent / dimethylformamide / 20 h / 20 °C

2.1: aq. AcOH / 16 h / 90 °C

3.1: 8.31 g / pyridine / 20 h / 20 °C

4.1: 81 percent / N,O-bis(trimethylsilyl)acetamide; TMS-OTf / acetonitrile / 16 h / 50 °C

5.1: DBU / acetonitrile / 18 h / 20 °C

6.1: 6.32 g / NaOMe / methanol / 16 h / 20 °C

7.1: 91 percent / pyridine / 1.25 h / 20 °C

8.1: 31 percent / aq. OsO₄; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol / 19 h / 50 °C

With pyridine; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1039/b307667a